1. Field of the Invention
This invention relates to a novel series of 5-endo-(3-indolecarbonyloxy)-[amino(lower)alkyl]-bicyclo[2.2.1]heptane-2,3 -di-endo-carboxylic acid imides possessing anti-arrhythmic and/or anti-fibrillatory activity.
2. Description of the Prior Art
A. British Pat. No. 1,042,840 describes compounds having the formula ##SPC3##
In which each of R' and R" represent hydrogen, or together an alkylene group having 1 or 2 carbon atoms, and R represents an alkyl group having 6 to 18, preferably 8 to 12 carbon atoms in a straight chain as having particularly advantageous properties as functional fluids.
B. U.S. Pat. No. 2,393,999 describes the compounds having the formula ##SPC4##
As being an effective insecticide.
C. U.S. Pat. No. 2,424,220 describes the compound having the formula ##SPC5##
As being an effective insecticide.
D. U.S. Pat. No. 2,462,835 describes the compound having the formula ##SPC6##
In which R is alkyl, alkene, aryl, substituted aryl, alkynyl, etc. as insecticides.
E. Culberson and Wilder, Jr., J. Org. Chem., 25, pp. 1358-62 (1960) report the preparation of compounds having the formula ##SPC7##
In which R is CH.sub.3, C.sub.6 H.sub.13 or hydrogen.
F. Rice, Reide and Grogan, J. Org. Chem., 19, pp. 884-893 (1954) report the preparation of compounds of the formula ##SPC8##
In which R is alkyl and their subsequent reduction with lithium aluminum hydride.
G. Worral, J. Am. Chem. Soc., 82, pp. 5707-5711 (1960) report the preparation of compounds having the formula ##SPC9##
H. German Auslegeschrift No. 1,179,205 reports the preparation of compounds having the formula ##SPC10##
In which the bicyclo[2.2.2]octane ring system is saturated and/or substituted, R and R.sup.1 are alkyl or alkenyl groups of 1 to 5 carbon atoms, or when combined with the nitrogen a heterocyclic ring. R.sup.2 is a (lower)alkyl group, n is a number of 2 to 5 and X a halogen anion. The quaternary compounds are described as having therapeutic properties in the treatment of cardiovascular disease, specifically high blood pressure.
I. U.S. Pat. No. 3,850,922 disclosed and claims the compounds having the formula ##SPC11##
wherein R.sup.1, R.sup.2 or R.sup.3 is H, Cl, Br, F, (lower)alkyl, nitro, OH or (lower)alkoxy, n is an integer of 2 to 4 inclusive and R.sup.4 or R.sup.5 is H, (lower)alkyl or when taken together with the nitrogen a radical of the formula ##SPC12##
in which R.sup.6 is (lower)alkyl; or a pharmaceutically acceptable acid addition salt thereof as anti-arrhythmic agents.
J. U.S. Pat. No. 3,850,921 discloses and claims the compounds having the formula ##SPC13##
wherein n is an integer of 2 to 4 inclusive and R.sup.4 and R.sup.5 are H, (lower)alkyl or when taken together with the nitrogen a radical of the formula ##SPC14##
in which R.sup.6 is (lower)alkyl; or an acid addition salt thereof as intermediates in the preparation of the anti-arrhythmia compounds found in U.S. Pat. No. 3,850,922 supra.